Hydrochloric Acid → HCID 13316896, compound

HRID 2295521Notes

Reaction equation

HRID 2295521 reaction equation
Cl.C([S:5][CH2:6][CH2:7][C:8]([N:10]1[C@H:14]([C:15]([NH:17][C@H:18]([C:21]([OH:23])=[O:22])[CH2:19][OH:20])=[O:16])[CH2:13][S:12][C@@H:11]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[OH:30])=[O:9])(=O)C>O.N>[OH:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C@@H:11]1[N:10]([C:8](=[O:9])[CH2:7][CH2:6][SH:5])[C@H:14]([C:15]([NH:17][C@H:18]([C:21]([OH:23])=[O:22])[CH2:19][OH:20])=[O:16])[CH2:13][S:12]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13316867HCID 13316867, compound

Product 1

HCID 13316896HCID 13316896, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 12896473Azane;hydrateSolvent

Procedure

In 10 ml of 28% ammonia water 0.5 g of (2S)-N-[(2R,4R)-[3-(S-acetyl-3-mercaptopropanoyl)-2-(2-hydroxyphenyl)-4-thiazolidinyl]carbonyl]serine is dissolved. The solution is stirred at room temperature for 30 minutes, and acidified with hydrochloric acid after removing excess ammonia. The separated oil is extracted with ethyl acetate. The organic layer is washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and ethyl acetate is removed to give 0.4 g (88%) of the titled compound.

Workup

  1. customafter removing excess ammonia
  2. extractionThe separated oil is extracted with ethyl acetate
  3. washThe organic layer is washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate, and ethyl acetate
  5. customis removed

Sources & evidence

ORD record
ord-3a38fe4b66034452ab42f6eb7bc45767
Source dataset
uspto-grants-1984_01
Patent number
US04425333

Reaction notes

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